Would you hire yourself? How lottery dreams can offer reality check for your career

Winning Mega Millions could offer chance to buy your existing company — would you hire workers that have the same skillset — and mindset — that you have?

It’s easy to imagine what we would do if we won Tuesday night’s $1.5 billion Mega Millions lottery. And while simply saying, “Take this job and shove it” may be high on your wish list, here’s another possibility some might choose: Buying the company they work for.

Who wouldn’t want to show the boss that they can do the boss’s job better than they can.

The possibility creates an interesting self-check on your career.

Simply put, when you become the boss, your first job will be to hire someone to serve in the position you used to have.

It leads to what should be a deeply self-reflecting question: Would you hire someone who has the same skillset — and same mindset — as you do?

Regular readers know we’ve done this story before. That’s OK. Any executive coach would tell you that you should take stock in your career every few years.

With that, here goes: Four questions to ponder about the person who will fill your current position — questions that really will show you where you stand in your present workspace:

  • Artificial intelligence — are you up to date? AI is something for the tech people … or the young people. It’s something that doesn’t apply to my job — and, by the time it does, I’ll be out of this role. Sound familiar? It’s what many executives thought about social media a decade ago. Consider this: It’s what many executives thought of computers (even Microsoft Word) a generation ago. Would you hire someone with this mindset today? If this is how you feel, perhaps it’s time to rethink your position.
  • Work from home: Do you know who is proving to be the hardest group to get back to the office? Midcareer folks. The ones who found out how much they like being able to have dinner and spend time with their families — the ones who relearned what they already knew: Commutes stink. If your job involves a strong commitment to the office, it needs to make sense to invest in a midcareer hire. Perhaps you should consider a recent grad or — gasp — an older worker as your replacement. Ask yourself: Would that make sense for your current employer?
  • DEI and B: Don’t know what the “B” stands for? It’s “Belonging.” Think this is part of the alphabet police taking over? Think again. Despite the recent Supreme Court ruling and a backlash against affirmative action, the hiring of a more diverse workforce (don’t forget the neurodiverse) isn’t going away. And it shouldn’t. DEIB not only matters to the success of your company (every single study proves it), it matters to hiring and retention. Smart companies aren’t hiring people who are willing to accept diversity — but those who embrace it. Ask yourself: Would you hire someone who thinks like you?
  • Passion for the job: This used to be an easy one — find someone who is passionate about their role, and you’ll have a happy (and productive) employee. (That is, one who willingly will work unpaid hours.) That idea isn’t necessarily holding true, post pandemic. Given a reprieve, many workers found that their work-life balance was out of order — which led to burnout and, ultimately, less productivity. It may seem counterintuitive, but finding an employee with better balance may be a better fit. After all, studies have shown a four-day work week does not corelate with a drop in productivity.

There it is: Four things to think about … while you think about what you’ll do when you win the billion-dollar lottery.